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Electrochemical 1,2-Migration Reactions Mediated by Vitamin B12 Derivatives

  • Yoshio Hisaeda

Abstract

Electrolyses of an alkyl halide having two ester groups and one phenyl group on the β-carbon atom have been carried out under various conditions in the presence of a catalytic amount of the hydrophobic vitamin B12. The migration of the pheny group was observed under the conditions forming a radical intermediate. The ester-migrated product was detected under the conditions forming an anionic intermediate. This is the first successful example in selecting a migrating group by electrolysis potential. A novel vitamin B12 derivative, which has phenylalanine residues on the peripheral side chains, catalyzed effectively 1,2-migration of the carboxylic ester in 1-bromo-2,2-bis(ethoxycarbonyl)propane at −1.0 V vs. Ag/AgCl under irradiation conditions.

Keywords

Radical Intermediate Alkyl Halide Migrate Group Carboxylic Ester Phenylalanine Residue 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Yoshio Hisaeda
    • 1
  1. 1.Department of Chemistry and Biochemistry, Graduate School of EngineeringKyushu UniversityHakozaki, Higashi-ku, FukuokaJapan

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